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Dear Debra
Dear Debra, Advice Columnist
Category: Relationship
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Experience:  I have been an Advice columnist for 14 years. My column is published weekly in local newpapers.
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Hello Based on the nature of the question, I really need a particular demographic to reply: an attractive woman with whom many men take (or have taken in the past) an active interest. Everyone knows what I'm talking about, here... I'm training a client with whom I'm falling for in a big way. We have worked together a couple of months and will stop in about another month. She's one of those types that every man wants and every woman wants to be. I know she enjoys my company immensely (she's said so multiple times) but she has a brainiac pretty-boy boyfriend who could have almost anyone he wanted. They've been together 2 years and argue quite a bit. He doesn't want to give up smoking pot or other drugs (he's well-employed, making good money) for her and claims that he will be a totally hands-off father (which she does not like one bit). I'm 44 (divorced, no kids, but still a boy who hits the gym 6 days a week) and she's 28. In my younger days, I was a bit of a player, and know how to talk to women. She knows for sure that I would make a great father. But again - her boyfriend is kind of like the LeBron James of our demographic. Yeah, a little bit of a selfish dickhead, but what woman wouldn't be willing to be with LeBron? Because she worked with me intensely for 2 months (and paid me a significant amount) I've begun meeting her briefly for free when its convenient for me (which it often is) and we've now had dinner together a couple of times. We have intense conversations that go all over the place. I know she enjoys herself. Last night, she talked about reading the 5 "languages" of love and how her two languages (words and physical affection) don't happen with her boyfriend (who provides services and small gifts). Of course, I do 4 out of 5, especially words and affection: I fight NOT to tell her how smoking hot she is. I'm going to have to wait at least a month before doing anything about this (when her "project" is finished) and its starting to get to me. At this point, I'm really wondering whether I'm barking up the wrong tree? Would a smart, beautiful woman with the world at her feet be willing to leave douche-Superman for a cute but definitely older guy? I know she knows I would make a great husband/father to someone, but she's never done any flirting, touching, hugging, or anything like that with me. I don't think she's the oblivious pretty-girl type who thinks that I'm "just being nice". She has a degree from a top-10 business school. I know she would never cheat on her boyfriend (he hasn't asked her to marry him) but I do think she would be willing to leave him for the right guy. This might sound strange, but my descriptions are quite accurate. For example, the brainiac has a Masters in Financial Engineering from Stanford. My client can easily be a super pretty, make-up free, lean, mean machine. She's no joke. Do women like that really end up with good guys like me? I'm just no Superman... Any thoughts would be appreciated. p5owgq2

Hi, I'm Josie and I am a moderator for this topic. I sent your requested professional a message to follow up with you here, when she is back online.

If I can help further, please let me know. Thank you for your continued patience.
Thank you for your question. One thing I see is when a women is interested in a man they drop little hints. They don't always directly come out and say that they are interested or come out and talk about their feelings, so they drop hints. One thing she was talking about was the five languages of love. She is telling you basically what her boyfriend is lacking. That means she is not totally happy with her boyfriend, she feels their is a few things lacking when it comes to the type of man she is looking for. He can be the most attractive guy in the world, but their also has to be that emotional connection. When someone truly loves someone they do not see flaws. They just love the person. people fall in love with people's personality and often do not see how people look on the outside. It only takes one thing some times for a person to fall in love with someone. If you look at what she was talking about she is talking about the language of love. This has nothing to do with work, so this becomes her way of telling you what is important when it comes to love. You asked if women like this end up with guys like you that are nice or course they do. She is a very successful women that knows what she wants in life, she is very settled in her life. She sounds lie she enjoys your company and you both have gone to dinner a few times. Even though she has not hugged, touched or did anything to show you she is interested that is not how people approach relationships. Some people do not want people to feel pressured or uncomfortable so they keep their distance, but drop hints like talking about the language of love that was a huge sign she is interested. When she talked about the 5 languages of love she wanted you to respond and tell her about how you are in relationships. I feel she wanted to know if you were interested in her and what a relationship would be like with you. Also if two people are happy and in love in a relationship they find no faults so when she mentions her boyfriend she would talk like there was no problems and tell you how much she loved him. But I feel she is telling you his flaws because she is looking for someone that fits everything she wants in a person. Her boyfriend can be everything someone would want on the outside, but it does not mean he has the personality she is looking for, she might be looking for more. I would take things slow and look for hints that she talks about. Anything that is not work related is her opening up too you. Thank you again for your question.
Dear Debra, Advice Columnist
Category: Relationship
Satisfied Customers: 1852
Experience: I have been an Advice columnist for 14 years. My column is published weekly in local newpapers.
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Customer: replied 3 years ago.

Thanks so much. Very informative. Any quick thoughts about the age difference (44 vs 28, although I have very "young" energy).

Thank you for your question. Where her life is very settled and she has accomplished signs much. I feel the age would not matter too her. The reason why is I feel someone older would also know what they wanted in life and I feel that would catch her attention. She would be looking for someone that knew what they wanted in life, someone that is also successful, but she would also need someone that would understand what she needed in a relationship. This is why she mentioned the five languages of love. The two her boyfriend are missing is the two she is looking for in a relationship. If he buys her things he is someone that shows his affection through gifts and that is because that's all he knows. Usually people who do that are often not affection. An example would be they don't hold hands, hug, cuddle, some times people like this don't often kiss. She could be looking for a more romantic side. He might not come right out and say he loves her. She is looking for someone that will tell her you look nice today in that outfit. She needs someone to see who she is on the inside. She is an attractive women who wants someone to notice the person she truly is. Her boyfriend might be more concerned with himself then her. The way you describe him, he might be someone that spends a lot of time maintaining his appearance and not enough time thinking of her wants and needs. I am sure she likes having dinner with you and just having an intelligent conversation. I think she is looking for someone that will show her how special she really is. I feel age will not matter because she is seeing you for you. She is not looking at your age, she only sees you. Thank you again for your question.

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